Palladium-Catalyzed Hiyama Cross-Coupling of Heterocyclic Phosphonium Salts with Arylsilanes

We report herein the palladium-catalyzed Hiyama cross-coupling of heterocyclic phosphonium salts with diverse (hetero)arylsilanes through C-P bond cleavage, providing an alternative approach for the highly regioselective functionalization of pyridines and relevant nitrogen-containing heterocycles. This silicon-based protocol is amenable to gram-scale synthesis and also applicable to the late-stage functionalization of pharmaceutically relevant complex molecules.